Issue 89, 2012
From the journal:

Chemical Communications

Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide†

Yawei Tu,a   Liejin Zhou,a   Ruifeng Yin,a   Xin Lv,*a   Robert A. Flowers II,b   Kimberly A. Choquette,b   Huili Liu,a   Qingsheng Niua  and  Xiaoxia Wang*a  

* Corresponding authors

a Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China
E-mail: wangxiaoxia@zjnu.cn, lvxin@zjnu.cn

b Department of Chemistry, Lehigh University, Bethlehem, PA 18015, USA

Abstract

The radical cyclization between aliphatic acyclic esters and alkenes was achieved unprecedentedly in the presence of allylsamarium bromide with HMPA and H2O as additives. The cascade radical cyclization–ring-opening–anionic cyclization allowed facile and efficient access to 2-(2-hydroxyalkyl)cyclopropanols from readily available materials.

Graphical abstract: Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

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Article information

DOI
https://doi.org/10.1039/C2CC34630C
Article type
Communication
Submitted
28 Jun 2012
Accepted
18 Sep 2012
First published
19 Sep 2012

Chem. Commun., 2012,48, 11026-11028

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Study on the coupling of acyclic esters with alkenes – the synthesis of 2-(2-hydroxyalkyl)cyclopropanols via cascade cyclization using allylsamarium bromide

Y. Tu, L. Zhou, R. Yin, X. Lv, R. A. Flowers II, K. A. Choquette, H. Liu, Q. Niu and X. Wang, Chem. Commun., 2012, 48, 11026 DOI: 10.1039/C2CC34630C

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